All I know is what I have been told about my early life. I am the youngest in my family of seven children and the only boy. My sisters are about 18 months apart and are Margaret, Catherine, Ann, Sara, Mary and Joan, my name is Matt, short for Matthew. I was born in 1966. I grew up in a small, middle class southern town. When I could remember, I remember I did not have a father. My mother told me my father left, and that was that. My family was my sisters, my mother and her sister. My mother was the administrator of a small hospital. She provided well for our family. My aunt worked in real estate and helped to pay the utility bills and provide for some of the extras that a family needed.
My first memory as a boy was standing in the bathtub. I must have been four years old, my youngest sister Joan was around six. We were standing in the tube waiting for the bubble bath to bubble up. I was standing there naked with my wee-wee showing. My wee-wee was not big, but it stood out causing me to noticed I had one and Joan did not have a wee-wee. Noticing the difference, I asked my mommy why. She told my I was a boy and boys had wee-wees and girls did not. That is all she said on the subject. I tucked my wee-wee between my legs trying to look like Joan. I told my mommy that I was a girl, Joan giggled, mommy laughed and so did I. I did the tucking trick a lot. Every time I was naked and one of my sisters could see me, I would tuck and pretend to be a girl. I wanted to be like them. All my sisters got a big laugh out of my tucking trick.
They would say, "Oh I see your wee-wee." I would turn around tuck my wee-wee between my legs and then show that I was like them. I would say, "Look I am a girl" and I would prance round emulating my sister.
The next thing I remembered was my Aunt yelling at me for leaving the toilet set up. I do not remember who taught me to pee standing up like most boys. Like most boys, I did not pay attention where the pee was going and sometime missed the pot. I did not remember ever told to put the lid down after every use. Well I guess one morning my aunt went in and sat on the porcelain rim and was very upset. My mommy told me to always to sit down to pee thinking this would be the best way to make sure that it did not happen again. That little advice was surly useful because I did not have to worry about leaving the toilet seat up, I still do not know what the big deal about the toilet seat. Half the time it is up or halt it is down, I have to lift it up to pee, or it is just as easy to have her lower it to pee. Today when I go to a public restroom, I use the stalls and not the urinal.
Sunday was laundry day, and I remember watching my mother fold all the clothes of my five sisters. I remember seeing white panties, pink panties, white bra and some colorful bra and panties that belong to my aunt. When my mother was not watching I would fall into the fresh out of the dryer clothing and felt the warmth surrounding me the smell of clean cloths. I would feel the silky touch of my aunt's undergarments. The warmth of the clothes felt like when my mother would hold me in her arms, and I felt safe and secure.
My family was large leading to some challenges growing up. Every year our cloths passed to the next younger child, from one sister to sister to me. For the first years of my life, what I got was Joan's clothing, panties, her girl jeans and tee shirts in pink, purple or green. From an early age, I was given girls underwear to wear. It did not matter; I did not know the difference in the underwear. I always sat down to pee not need the opening that boys underwear had. The panties were the standard white cotton panties with bows. Some of the panties were pink from washed with something red. Wearing pink girls' panties was never an issue in kindergarten. No one noticed, if someone did, I do not remember anyone making an issue.
My family was casual when it came to our personal habits. The bathroom door remained open unless when one of the girls was getting ready for a date then she would spend hours in the bathroom making the rest of us wait until they were pretty for their date. Therefore, I have visions of my sisters in various state of dressed and undressed and can remember comparing the differences in breast size and pubic hair. I started to notice my sisters' breasts when I started the first grade, my oldest sister Margaret was fifteen. I was walking down the hall the door to the bathroom was open, naturally, and I looked in. Margaret my oldest sister was standing in front of the mirror looking at her breasts. I watched as she put on her bra, backwards and twisted it around slipping her arms through the straps and adjusting each breast. I remembered that each year before the start of the school year the big event would be one of the girls would be given her first training bra. Ann who was about 12 received her first training bra. It was a big deal with much giggling. I remember thinking that when I was older, I too would receive a training bra.
I had curly hair, and it was kept long, up to my first year in school when it was all shaved off. I cried that night because I missed my shoulder length hair that made me look like my sisters, now I look not like them... When I was in first grade Margaret was starting so far, and she was using make up. I would sit there watching her take this brush and put it on the eyes and this tube on her lips and would see my sister transformed into a young woman. She would play a game with me and put lipstick on me, and I would go around the house displaying to my sisters that I was like Margaret and making faces and sticking my tongue out. Margaret once did my entire face, and I looked like a raggedy Andy doll with bright red cheeks. That got many laughs.
As a boy, I did not realize there were two genders. There was no man around the house. I did not know to stand to pee but acted like my sisters. I laughed like them in a girly giggle. I pranced round like them walking and swaying my hips. I hid my wee-wee from my sister's site because I wanted to be like them. I adored my older sisters and wanted to be look them, walk like them, talk like them.
I had long curly hair when I was young. In our early family portraits, you could not tell I was a boy. As in life, everything changes. Prior I started first grade my mother took me to the barbershop and had cut off my curls. I cried that night because I did not look like my sisters. When I started first grade I was still wearing Joan's hand me down panties and girl jeans, which zipped differently the other boy's jeans. I was not aware of the different in how girl's jeans and boy jeans fasten. My mother did have to buy me boy's shoes. My feet were bigger than my sisters were, and there was no hand me downs that would fit.
I remember when Mary got her first period and how embarrassed she was to have stained her panties. I overheard my mommy tell Mary that this was normal that all women will bleed and that it is a curse, but it allows you someday are a mother, so it is worth the trouble. Mary was instructed how to use a pad and to be sure that when it was her time of the mount to remember carry them in her purse. I now realized why my sisters carried purses.
When I was in first grade I started to hang out with what I was comfortable, and that was with the girls. I played hopscotch, did the jump rope, and the hand clapping and chanting with the girls. I had the chance to play softball, tag, or other boy's games, but I preferred to sit with the girls and watch. When I did play softball, I through the ball like a sissy and everyone laughed. As I advanced through the grades, I became aware that I was different from the other guys. I did not talk like a guy, I did not walk like a guy. My clothing was different the other guys. I remember telling my mother when I was in third grade that I was differed from the other boys because I was not dressed like them. My mother took me out shopping for my first boy jeans, but I still wore panties. I was nine.
Going into the fourth grade, I was being teased by the guys for playing with girls. It did not take me long to understand that it was better to be alone not playing with the girls, or not playing with the guys. The teasing was reduced. Starting the fourth grade, I found my best friend, Billy an older boy who was left back a grade. The school he was from was not as advanced as ours was. Billy's reading was not good causing him to have to repeat the fourth grade. He was new at our school, and I was alone, so we became friends. I was ten and Billy was 11 and half. Another reason we became friends, Billy protected me from the others because the way I talked and acted. I helped Billy to read. What I did was to read to him, so he could answer the questions in class the next day. Every day after school we would spend time playing in the woods in an undeveloped part of town. We found a pond and sat there in the early spring reading about history and science. The first day in the woods, Billy said he need to take a leak, I did not know what this meant as Billy stood up and walked to a tree. He was in plain sight, and I watched him pee on the tree. I never saw man or boy do that before, and it is something I remember to this day. Billy asked me if I needed to take a leak, I said no. The next day the same thing happened, this time I decided to do what Billy did. For the first time in my life I stood, like a man, to pee. It was wonderful. We both stood there pissing on the same tree, our streams crossing and seeing who could pee higher. Of course, Billy could because he was taller than I was.
It was when I was standing next to Billy peeing, Billy noted that my underpants were pink and did not have the opening where you would slide your wee-wee through to pee. I had to lower my panties and hold them down below my balls in order to pee. When we were finished, peeing Billy asked to see my underpants and not know why, but without hesitation, I dropped my jeans to reveal my panties with lace around the legs and the waist. Billy showed me his underwear, for the first time I realized there is a difference. I joked with Billy and said that if he wanted I could give him a pair of panties and he could look like me. We both laugh at the joke. The next day Billy gave me a paper bag with some of his old underwear. I was excited and please that I would be dressed like him. I wore Billy's underwear during the week, but there was not enough to go the week so by the weekend I wore panties again.
Billy noted that I tossed the ball like my sisters. One day down by the pond, he brought two gloves and a baseball. We spent the afternoon playing catch, it was not long that I had a good arm in throwing the ball.
In the woods, we did guy things played cowboy and Indians, cop and robbers and army. I made sure that we did our reading assignments, so Billy would not get in trouble at school. We even skinny-dipped in the pond where the water was cold and out wee-wee, and balls would shrink. Then as we lay in the sun drying off allow our wee-wee to return to normal size. Billy being about 18 months older than me was taller than I was. He started have some pubic hair start growing around the top and sides of his wee-wee.
Being older Billy had and a sex discussion with his father and he shared some of the sex details with me. I did not understand all that he told me especially about how the wee-wee would slip inside the girl and nine months later, she has a baby. Billy had an older bother and no sisters. I told Billy all I know about my sisters, how I saw them naked and knew that they had a period every month. Between the two of use, we had a good understand of the differenced between a girl and a boy.
I was in the fifth grade, eleven years old when I woke up and thought I had wet the bed because I was wet between my legs and there was a wet spot on the sheet. I must have woken my mother up, and she came in to clean me up and change the sheets. I was to embarrass to ask what happen and went back to sleep. The next night it happens again, and I asked my mother what was happening. She said I was growing up and that my body was changing. I got the sex speech that Billy had told me a year early, he left out about wet dreams. My mother had some advice for me. My mother told me that before bed if I did not want to have a wet dream to play with my wee-wee and I would cum where I cold avoid having a wet dream. I tried that a few times and it took a long time to get off. I did not have anything to help me visualize about jacking off. I did not know how to have sex with a woman. I did not look woman as sex objects. The next morning at breakfast, I told my mother that it had taken me a long time to "ejaculate". My aunt was standing there and reached under her skirt, pulled off her red panties and tossed them to me. Her panties were warm, smelled of perfume and were silky with lace and bows. She said to rub this on your wee-wee, and I would come faster. I put the panties in my draw with my hand me down panties, next to my boy underwear and now my first pair of woman panties. My mother just looked at her sister with a look like, "why did you do that".
I thought of my aunts panties all day and could not wait to go to bed. That night as I lay in my bed, I wrapped my wee-wee in the silky panties and started to stroke my little wee-wee. It was an amazing feeling, much better than with my hand. In five minutes, I had exploded in the panties keeping the mess contained and not wetting the sheets. The next morning I washed the panties out and hung them up in the shower just like my sisters. When I arrived home after school, I went in the bathroom to recover my frottage, but it was not there. I thought that one of my sisters took my panties, I was angry. I went into my room, open my drawer to find the panties folded, and place next to my other panties and there was a second pair just like the fist but black.
I went to bed early just so I could cum and feel so relaxed after my climax. I had loads of cum in the panties. Instead of waiting to wash them in the morning, I did it that night. The next morning they were dry, returning to my drawer.
If the weather was bad, we went to Billy's house or to the library. It was a few days after my first wet dream, I told Billy about it. I told him what my mother told me to do. Billy got a smile on his face and told me that he had been jacking off for over a year. He asked if I wanted to see his brother's jack off magazines. I said sure. We went into his bother room and under the bed were several magazines such as Hustler. The pictures were as graphic as you could want to see. I could see what a pussy looked like. Up to this time, all I saw of my sisters was a slit and their pubic hair. Now I saw everything. We sat on the floor looking at every picture and every ad for sex.
Billy was rubbing his crotch looking at the photos, I was aware that I was hard and felt the need to rubbing my wee-wee. I had seen Billy's cock many times in the woods when we pissed or when swimming. Billy said, "You have a wee-wee because you are small. I have a cock because I am big." I felt embarrass because he kept referring to my wee-wee as small wee-wee or little wee-wee. We sat there looking at the magazine commenting on the size of these breasts and look at that pussy. Billy unzipped his pants and pulled out his cock. I was surprise, Billy's cock was erect and huge. It was three times as large as mine was and very thick. I measure my wee-wee, and it was one inch when I was ten, two inches when I was eleven. One day I knew I would be as large as Billy. His cock was thick too with the head exposed being bright pink. He said he was "circumcised". Billy said that some boys had the extra skin that slides over the end of their cock. He said that they Jewish boys when they are thirteen, the extra skin would be cut off. We looked at each other and said "ohooooo" at the same time. I took out my little wee-wee, felt a little ashamed but Billy said that in a year, I would be as big as him. As we looked at the pictures we Billy rubbed his cocks, I rubbed my wee-wee. I watched Billy touching his cock, I would do the same with my wee-wee. I was being a copycat to his every move. He started to cum. He squirted a long squirt of white liquid a good three feet that landed on my arm. It felt warm, wet and was sticky gooey. The next squirt was off to one side and landed on my leg, the third squirt did not go as far and landed on my feet. The sight of seeing Billy come was so erotic that I came and my cum shot all over the hustler magazine, causing Billy to say "shit", got up and found some tissues to clean up the mess. The one picture was ruined, Billy he tore it out of the magazine. He gave it to me and told me to toss it out on my way home. We cleaned up the room, our mess and went to Billy's room. We did not say much about what we did in his brother's room. I read to him out the next day's reading assignment.
That night I reached into my pocket and pulled out the hustler picture that I was to toss. I now had panties and a picture to jack off to and came quickly. Before it had taken me over a 15 min to come and now with the photo and panties, I could shoot my load into my silken panties in two minutes.
The weather was bad the next day as we ended up at Billy's house and in his brother room looking at the jack off magazines. This time there was one magazine called SheMale and had a photo of woman with cocks. This was confusing to me. Billy said some people were neither men nor woman but were shemale. The pictures were exciting and still confusing. The SheMale did not seem to have a slit like a woman just a cock and balls with big breasts. Billy started to jack his cock. I started to jack mine. I notice that his cock was all shiny and that some white fluid was dripping out of his piss hole. He said it was pre-cum and that he used it to lube his cock. Being younger, I did not have any pre-cum yet. Sensing that I needed something to help me jack, Billy said I could have some of his. He moved closer as I held out my hand. Billy squeezed a drop or two of pre-cum out of his cock. I rubbed it on the head of my cock. With a few stokes, I started to cum. I had a tissue in my hand so did not create a mess as I did the day before. The touch of Billy's pre-cum in my hand, and lubing my cock with it was sensual. Billy gave me his pre-cum, I accepted it as something special. After I cam quickly, Billy continues to jack sitting directly across from me. I did not think was in the line of fire until he exploded and this time it was not on my leg, or arm. The first squirt hit my face, it was warm, wet gooey cum. The second squirt was on my chin and neck and the third squirt on my chest. I was a surprise at how quick it happened. Billy was watching to see my reaction. Billy said he did not mean to cum on my face and smiled. I remember the look in his eyes, it was the look of pleasure or satisfaction having hit my face. I smiled back with a look of acceptance and giggle like a girl. In a strange way, I felt I should be the one to receive Billy's cum. We were the best friend and having him squirt his load on me was just a benefit of our friendship.
It was the weekend, and all my boy underwear was dirty. I could wear my pink cotton panties or could try on my silk panties. I selected the black lace panties. They felt sensual touching my wee-wee, my wee-wee sliding up and down inside my panties, my wee-wee was semi erect all the time. I knew I was aroused all the time and knew if I touch my wee-wee I would cum quickly and would be rewarded with that Europhobic feeling. It was Saturday I had finished my chores. I hurried over to Billy house, so we could play again.
Billy greeted me with a big smile on his face; we got a couple of Cokes out of the refrigerator and sat in the den. We were watching TV, nothing special, flicking the channel seeing if there was anything interesting to watch. It was Saturday and many cartoons but nothing interesting. Billy asked, "What do you want to do?'
I was hoping that we would go to his brother's room but did not want to suggest that so said, "I do not know what you want to do?"
Billy seemed to be hastate to suggest that we go to his bother room. When we were not in his brother's room looking at the magazine and playing with our cocks, Billy did not talk about what we did. It was as he was a different guy. When we were in his bother room and looking at the magazine, we always were jacking. He would joke with me, would tell me fantasies about how nice it would feel to slide his cock in a real pussy. He would tease me and said, "Matt you have a tiny wee-wee it would never slide into a pussy. You are going to have to use your hand until you have a real cock."
I would laugh and say, "Oh This time when started to play I took off my pants to show Billy my black lace panties. He just stared at them and said, "Cool, cool, so cool". He even reached out and touched my panties to feel how smooth they were. I was sure this was the first time he every saw woman panties before, I smiled and was a little excited about showing off my secret. Billy was looked at me dressed in black lace panties and asked me to take everything off but the panties. I had a very white and thin body, not a boy shape but more on the feminine side. He said, "Matt you look very sexy, I want to come on you again."
I protested by saying, "Oh, that is yucky."
Billy replied, "Come on your little pussy, you can wipe it off. I want to see how far I can shoot and hit a target. Smile you are my target."
I could tell that Billy was not going to take no for an answer. His cum would not be on my face long. I could wipe his cream off my face. It was something for me, I could not say no. Besides, I did not know why but I wanted to see him squirt again. I wanted to watch him play with his cock and then wanted to see him cum. I agreed, "OK, but only this one time and I will wipe it off, ok".
Billy said, "Lie down and rub your panties. Pretend you are a girl. Pretend you have a pussy, rubbing your pussy."
I reclined on the floor looking up at Billy, "like this?" I tucked my wee-wee between my legs and rubbed the area. I was naked except for my black panties, at my age was flat chested, skinny, and looked like my sister. All I needed was my long hair. I am sure that Billy saw me the same way. Billy stood over me jacking his cock as I looked up watching. I had a fascination in watching Billy for several months we played with our cock, with me copying his hand action finding the best way to come. Sometimes he would grab his cock in his hand and touching his forefinger and thumb together making a ring and with the other three fingers, he called his pussy hand. Sometimes he would rub his cock with one finger around the head of his cock, then tickling the area under the head. Sometime he would put both hands together and move his hips in and out and he would hump his hand. Billy would start jacking his cock faster it would get very hard, and the head would turn from pink to purple. He would yell, shooting his cream all over me. The first few times his cum went all over and did not land on my face, but with some practice, he could aim and hit my face. He took such pleasure in seeing his cream on my face and dripping down my chin. When we were in his brother's room, he would call me Cindy. I asked him why and he pulled out one of the shemale magazine and opened it to a page where the girl was named Cindy. Billy said I reminded him of her. When we were playing, he called me Cindy and I enjoy my feminism name. When we were not jacking our cocks we were just two normal guys and Billy would remind me to sit with my legs open and not together. He would tell me that I needed to walk like a guy and even told me to talk like guy. I developed two different ways to act around Billy, straight acting Matt and girly acting Cindy. I was Matt most of the time when around Billy. I did look forward to be Cindy. I enjoyed my guy time with Billy. I liked my Cindy time with Billy, so I could climax.
Billy asked me if I could bring next time a training bar to wear. He told me, he wanted me to be dressed more as he wanted a girl. I know that I could find a training bra somewhere and bring it the next day. It was Saturday again, I put on my red silk panties and the training bra, next my outer clothes. No one could see I was Cindy underneath and Matt on the outside.
I took my Matt clothes off and show Billy my red panties and my white training bra. He said, "Cindy you fucking bitch. Here is something I got for you," as he handed me a paper bag. I opened it up and saw hair, Billy had found a cheap costume wig for me. It was shoulder length, blonde and had curls. I put it on and looked in a mirror; I looked just like I did before my first haircut. I looked like one of my sisters with the curly blonde wig, the training bra and the red silk panties. Billy said, "Damn, Cindy you are looking good." Billy patted my rear. "Walk around for me," as he took out his cock and started to stroke his erection. I pranced around the room, swaying my hips and using my arms to talk, my wrists were limped. I said, "Oh Billy, you are so silly. Do you like my outfit? I got it just for you. Oh my, Billy that is a big cock you have. Are you going to cum for Cindy? Billy my man."
Billy said as he stood up, "Get on the floor you fucking bitch, lie on your back" I did as Billy told me. With that, Billy straddled my body with his legs, knelt down, he was sitting on my chest. In this position, I could not move and felt helpless. Billy's cock was just inches in from of my face. He leaned forward rubbing his cock on my face, slapping my face with his hard on. It hurt a little, and I wanted him to stop, but I did not say anything. Billy in a low voice, "Oh Cindy you are so pertly, and your skin is so soft. Do you like feeling my cock rubbing your face you? Cindy you are my bitch?" With that being said, he shot his wad on my face and did not miss, I was covered from forehead to chin. Billy was off of me, looked at my face with his cum all over, he smiled with pleasure and told me to go are cleaned up. I returned, the magazines were put away, Billy was not in the room. I still had a hard on and wanted to cum but got my Matt cloths. I put the wig back in the bag and went to find Billy in the den watching TV. I handed him the bag with the wig, and he told me to keep it, bring it when you again come tomorrow.
That night I went to bed, and with the lights off and alone I rubbing my cock with my panties and had a great big load and a warm feeling of well being. As I closed my eyes thinking about Billy with his cum all over my face, I felt satisfied. I also enjoyed Billy calling me his fucking bitch. I liked that.
Each day of the week, I would go to Billy's house. We would grab something to eat, watch TV and Billy would lean over and tell me to go up stairs. That was my clue to get dressed as Cindy. Billy quite watching me get undressed only entering the room when I was dressed as Cindy. He would enter his brother's room and say, "Cindy so nice that you could visit me. You look hot today." Today I had a surprise for Billy; I have stuff the training bra with tissues to give me the looks of breasts. Billy responded by saying, "Wow, Cindy you have tits. You look better every day." With that, he reached out and touched my fake tit, rubbing his hand on my chest and then holding me close to him. I could feel his hard cock against my body. Billy said, "What do you want baby, you want my cock?"
I responded in a frail, feminism voice, "Oh yes Billy."
Billy said in a demanding voice, "Well go ahead take out my cock you little cock bitch." I got on my knees, keeling in front of Billy, I unzipped his jeans and fumbled with is cock and finally freed it. This was the first time that I had touched Billy's cock. I felt strange and different. I could feel that his cock was warm, that his cock was hard and that his cock was silky smooth, almost as smooth as my panties. My fumbling with his cock must have been a turn on for him because as soon as I got his cock out he shot his load on my face. I looked up at Billy and could see a smile on his face as he wiped his cock across my face getting cum all over his cock and my face. Billy said, "Go get cleaned up your fucking cock bitch. You did well today."
I went to the bathroom, looked in the mirror, and saw my face. I loved the wig and curls. When I saw all of that cum on my face, I smiled. I rubbed it on my face and not know why I licked my hand tasting Billy's come for the first time. It was salty and not unpleasant at all. I smile at the girl in the mirror and said to myself, "Cindy you are lucky to have a friend like Billy."
When I return Billy was gone, I dressed as Matt and went down stairs. Billy got me a coke from the refrigerator and asked, "What do you want to do?"
I responded, "I do not know what you want to do?"
Billy said, "Let's go the Mall."
Walking in front of a dress store Billy stopped. Seldom did he say anything about our dress up activity but this time he did. Billy said, "Tomorrow I want you fully dress like that," as he nodded to the mannequin in the window dress in a blouse and skirt.
I responded, "Sure Billy anything you say." I knew that I could borrow some of my sister's clothing. I went home that night, and while my sisters were cleaning up after dinner, I snuck into Joan's rooms. I went into her closet, and quickly found a skirt and a blouse. I tried to find one that I did not remember seeing wearing. I hoped she would not notice they were missing.
The next day I went to Billy house, he told me to go on upstairs he would be up in a minute. I got dress as Cindy. This was the first time for me to be fully dress. I enjoy looking into the mirror admiring my legs, the skirt and blouse and of course my curly blonde wig. I looked like my sister Joan only taller. Billy entered the room and immediately got a smile on his face. Billy said, "Cindy you are so sexy fully dress, I want to see you like this every time." I stuffed my training bra again with tissues and with the blouse I borrow, it was somewhat tight. The blouse stretch over my training bra giving me the illusion of nice tits. Billy said, "Cindy get on your knees." He moved, so he was standing in front of me. "Take my cock out," he ordered. I did as ordered. "Now, play with my cock Cindy." This was only the second time that I touched Billy and was not sure what to do. I know how to play with my wee-wee, and I have watched Billy play with his cock but to touch his cock was different. I grabbed his cock with one hand and slid my hand up and down. Billy moaned softly, "Yea baby, just like that, you are doing fine." I was amazed at feeling Billy's cock in my hand how warm, smooth and hard he was. I stopped and rubbed with my finger the area under the head and got a response that I was tickling Billy, I giggled like a girl. Billy started to moan again and started to move back and forth in my hand until in a second, he exploded. I aimed his cock to my face and got a face full of his wet hot cream. Billy looked down seeing my face covered with cream said, "Oh Sweet Cindy that was the best ever." "Now go clean up." I went to the bathroom, looked in the mirror, and enjoy seeing Cindy looking back with Billy's cream on my face.
We did not meet in the woods any more; I could not dress as Cindy there. Billy and I continued to meet after school and on Saturday. Each time we met in his brother's room, Billy would think of something new or different to try. I was now all about Billy and Billy coming. Billy did not want to see my wee-wee, I hid it just like when I was at home. I did not think our playing was odd or wrong. It was like when we played cops and robbers, or cowboy and Indians. I was pretending to be a woman, and Billy was playing himself, a horny teenager. We continued to play the rest of the fifth grade. Now I would give Billy a hand job while dressed as Cindy. Each time he wanted to see is cream on my body. I did not think this was a gay activity. We were just playing.
Beginning the six grade, I was now 12 and Billy was thirteen and a half. His had fully developed pubic hair and bragged that he was saving at least once a week. His cock got larger and thicker, I enjoyed feeling him get hard in my hands and coming when I jacked him off. I got a reward when I did a good job. I did not cum when I was with Billy but had to wait until I got home. I could visualize Billy, his cock and cum all over my face and that help me when I used my silk panties. Over the summer, I grew three inches taller, my wee-wee got bigger.
At the start, of the sixth grade and one day when I was Cindy playing with Billy's cock I said, "Billy, can I show you my wee-wee?"
Billy looked at me wired and said, "Sure Cindy show me your clitty. That was the first time he had referred to my wee-wee as a clitty. So I pulled up my skirt, pulled down my panties and revealed my wee-wee. Billy smiled and said, "Cindy I can officially say that you do not have a wee-wee anymore. Matt you now have a cock, and as Cindy, you have a clitty. Now make me feel good and slide your hands up and down my cock. I did as I was told having a big smile on my face. I have finally grown up and now had a cock and Billy was my friend who helped me be Matt when in public and helped me be Cindy when we were in private.
It was around Christmas time, I had dressed up as Cindy for Billy. Billy entered the room and said, "I have a surprise for you. I found this porn tape that you need to see." Billy turned on the TV and started the VHS play. The porn movie started where Billy had left off. It showed a guy sitting down who was very naked and that a woman fully dressed was kneeling. The man's cock was in her mouth. The camera angle changed to show a close up of her taking the head of his cock into her mouth. Then half of the shaft and finally he pushed her head down and all of his cock disappeared. The woman gagged and was let up but then pushed down again gagging. The action continued showing her licking his balls, sucking his cock until he shot his load into your mouth. She kept her mouth open until he was through coming. The video showed a closed up of her mouth. She swallowed; open her mouth to show that all the cream was gone.
I looked at Billy and said, "You want me to do that?"
Billy nodded his head and smiled, "You would enjoy it Cindy."
I protested, "Billy that is gay to for a guy to suck a guy's cock."
Billy said, "No it not, the video showed a man and a woman having oral sex that was not gay. That is normal when a man and woman have sex, she sucks his cock, and it is expected."
I responded, "But Billy, I am not a woman, I am a guy and a guy sucking a cock make me gay and I am not gay."
Billy looked at me and said, "Cindy you are dressed as a woman, when you suck my cock think of your self as a woman, then it is not gay." "Cindy you are my girl and when we are together you need to do certain things for me.""Besides no one will know and if no one knows they will not call you gay."
But Billy, "I pleaded." Billy looked at me straight in the eyes put his hands on each side of my face and pulled me close and kissed me on the lips. His lips were warm, soft and felt like something I have never experienced.
I said with a surprise, "Billy."
Billy put his finger to my lips and said, "Shush." He unzipped his pants took out his cock and said, "Cindy kiss my cock as I kissed you."
My mouth was open from the surprise kissed. I was not sure what to think about seeing my first porn video of oral sex. I did not want to be gay or do gay things. I had to make a decision and fast. Billy was right, when I was dressed as Cindy I pretended to be a girl and a girl can suck a cock, and it was not bad. It did not seem to be wrong, and Billy has been good to me. I said, "OK, Billy. Just so, you do not tell anyone. I will do it today, but if I do not like it, I do not want to do it again, OK"
Billy said, "Sure baby, just try it today. It will be ok. You can stop at any time if you do not like."
I got on my knees, and kissed the tip of his cock. He moaned a little, I continued to kiss his cock, up and down his shaft, then his balls. I knew I was teasing Billy, he deserved it for asking me to suck his cock. I kissed the head of his cock and remembering the video, I opened my mouth looking up at Billy. Billy guided his cock into my mouth as I closed my lips around his cock. Billy said, "Ohoooooo my Cindy that feels so good, do not stop." Billy urged me on by saying, "Oh you are a good cock sucker. Use your tongue and tickly may cock. Yes Cindy just like that." I was encouraged by his words. The more he told me what to do the more I wanted to do it. It did not feel wrong for what I was doing. I now moved my head back and forth allowing Billy's cock to slide in and out of my mouth just like in the porn video. Billy said, "Oh man, I coming." Billy came in my mouth, at first I felt his cock get very hard and that the head filled my mouth. Billy cum filled my mouth and tasted salty at first, it was warm, it was thick his cum was all mine. I opened my mouth to show him his cum in my mouth and then swallow just like the porn movie. I open my mouth to show him that I swallow his cum then looked at him and smiled. The taste in my mouth changed to something bitter but still was not unpleasant. I was very pleased with my actions, sucking my first cock and making a man come. It was a turn on for me. Just by using my mouth, I could make a person cum. It was exciting for me to know that I had this power. I also knew I would do this again for Billy. I realize I was the one with control over Billy climax. I could make it last a long time or move my head faster and get him to cum sooner. I would decide if he would cum on my face or in my mouth. I was in control, and if I said no, Billy would not cum at all.
About Easter break, I was dress in my sister short skirt and white knee-high stockings and white school blouse. I could have passed for any girl in the six grade. Billy gave me a bag that has some pantie hose. I have seen them many time hanging in the shower, have touched them but never had I put them one. Today Billy gave me a pair and told me to try them on. I did and enjoyed how smooth they felt against my body. I pulled them all the way up my legs and wiggled my bottom to get into the pantie hose. I turned around showing off my legs and rear to Billy who just smile and rubbed my legs and my rear. He showed me another VHS tape and said that I will enjoy this action. This time it showed a man and a woman, she was on her hands and knees. He was kneeling behind her. He was moving forward and back as she was moaning. Billy said, "Cindy she is in the doggy position and he is fucking her.
I responded, "Billy I do not want to do this. I do not want you to fuck me."
Billy smiled and said, "Silly Cindy, I do not want to fuck you, I just want to slide my cock between your legs, so I can feel how smooth the pantie hose are. You keep the pantie hose on and will be safe." "So Cindy get on your knees bitch."
I was not sure about this, but if I kept the pantie hose on, I guess it was safe. Billy always got his way. I would say no, then he would convince me different. Knowing that Billy would get his way, I said, "OK Billy, but no fucking me." I got on my hands and knees, looking up at Billy. I said, "You mean like this?" As I assumed the position. Billy moved to behind me.
Billy said, "Cindy, put your legs together, so I can slide my cock between your legs." I did as told and waited. Billy rubbed his cock up and down my crack and finally sipped it between my legs. He then proceeds to move his cock in and out, sliding between my legs. His cock was rubbing against my balls and my cock, exciting me. I knew that he was not fucking me, but it felt good anyway. Billy was holding my hips pulling me back on his cock. I wondered what a woman felt when she was fucked by a guy.
Billy fucked me faster and then came all over my pantie hose. I knew I was going to have to wash them before the next day. Billy patted me on my backside and said, "Cindy you are such a good girl and you have such sweet legs." I was glad we pretended to fuck, and pretending was exciting for me. I did feel like a woman in the porn video. Over the next few weeks, Billy would put me in different positions trying to find one that would excite him the most. He had me on my back and put my legs on his shoulders. He told me to lie on my stomach, allowing Billy to get on top. He did it standing up and even allows me to sit on top of him. I like that position a lot because I could decide how much of his cock would slide between my legs. Some time it was just a little, gut the head of his cock. Other times I would slide up and down to stimulate his entire cock shaft. He bent me over the couch, the kitchen table; he fucked me in every room of the house.
It was near the end of the school year and the six grade that Billy told me that his Father got a job in another town and that he would be moving when school was out. I could not believe what Billy was saying, my very best friend, the one that protected me from the other guys, my friend that told me about the birds and bees, my friend that I let come in my mouth. That night I cried, cried for my lost of my best friend. I did not know what I would do that summer and did not want to think about going to Jr. High School without someone to protect me.
On the last day of school, I shook Billy's had and stood tall as he told me. He called me Matt, leaned forward, and said, "Cindy, I will never forget you and you keep being Cindy when you can." He winks at me and said goodbye. It was years before we saw each other again.
I was not in the seventh grade 13 year old and had to make some decision. First, I decided that I was not gay and that need to be Matt. I decided to quit wearing my silk panties and my mother had bought me boys underwear. I was a smart guy, always had good grades and knowing I would figure out what I was going to do.
In the seventh grade, you had gym class and had to take showers with the other boys. I did not mind because I had a respectful size cock. I did compare with the other boys, and I was one of the larger one there. I also started to get my pubic hair my voice lowered, and I learned not to giggle like a girl but like a boy. I pissed at the urinals but at home had to remember to sit down to pee. I did not jack off every night and did not have any more wet dreams.
I was still a loaner at school, but no one picked on me, Billy taught me to stand up tall, and not to take crap from anyone. I got through seventh grade without any incident. Billy would send me a letter now and then said that school was not same, but he found a girl to read to him and put a smiley face.
I developed into a young man. Graduated high school and had a scholarship to a college a couple of hundred miles away from home. I had complete freedom but had a responsibility to keep my grades up. To make a little extra I had a job in the local bookstore where I met and knew many of my classmates. One day I over heard two freshmen girls talk about makeup and about putting on lipstick. I could not help myself and told them to forget the lipstick and to use your blush and then clear lip-gloss. They looked at me and said what I knew; I smiled and said, six sisters. From that time on, I would give out advice on clothing, makeup and dating. While I did not have a steady girl to date, I did meet a few my first year at school. I found them to be very dull and not able to carry on an intelligent conservation or so stuck on them selves that I considered them high maintenance.